If you were to tell a story about a late partygoer, you could mean someone who arrived long after the party started, or you might mean someone who died at a party. These very disparate uses of the word "late" can be confusing without the proper context. The reason that the word has two meanings goes back to the early use of "late" (pun intended). In the 15th century, the word was used to mean "recently." You can understand that by the phrase "of late." There are many examples that are now considered archaic, but we still use a form of it in phrases like "the latest comic from Randall Munroe." When referring to someone who died, the term "late" was originally only used for someone who passed away so recently that it might be news. But we strayed from that, and now say "the late Richard Harris," even though he died more than twenty years ago.
So the "behind schedule" definition has survived, and the "dead" meaning has been altered, but the in-between definition that meant "recently" has mostly fallen away. Read a rundown of how the word "late" has evolved over time at Mental Floss. Now, as far as the use of the phrase "the late, great..," that seems to have come about just because it rhymes and is therefore fun to say. -via Strange Company
(Image credit: Roman Eisele)